Comparison of dppf-Supported Nickel Precatalysts for the Suzuki-Miyaura Reaction: The Observation and Activity of Nickel(I)
Comparison of dppf-Supported Nickel Precatalysts for the Suzuki-Miyaura Reaction: The Observation and Activity of Nickel(I)
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DOI：
10.1002/anie.201505699
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发表时间：
2015-11-02
影响因子：
16.6
通讯作者：
Vinyard, David J.
中科院分区：
文献类型：
--
作者：
Guard, Louise M.;Beromi, Megan Mohadjer;Vinyard, David J.
与常用的Pd体系相比，铃木-宫仓反应的镍基预催化剂具有潜在的化学和经济优势。在这里，我们比较了Dppf配体在0，I和II三种氧化态下用于铃木-宫仓反应的Ni预催化剂。令人惊讶的是，在80℃时，它们具有相似的催化活性，所有体系在反应过程中都会产生大量的Ni-I。在室温下，一种易于获得的稳定的Ni-II预催化剂具有很高的活性，可以偶联合成重要的杂环底物。我们的工作最终证明，Ni-I物种与通常建议只涉及Ni-0和Ni-II络合物的反应有关。
Ni-based precatalysts for the Suzuki-Miyaura reaction have potential chemical and economic advantages compared to commonly used Pd systems. Here, we compare Ni precatalysts for the Suzuki-Miyaura reaction supported by the dppf ligand in 3 oxidation states, 0, I and II. Surprisingly, at 80 degrees C they give similar catalytic activity, with all systems generating significant amounts of Ni-I during the reaction. At room temperature a readily accessible bench-stable Ni-II precatalyst is highly active and can couple synthetically important heterocyclic substrates. Our work conclusively establishes that Ni-I species are relevant in reactions typically proposed to involve exclusively Ni-0 and Ni-II complexes.